Amphoteric derivatives of aliphatic polyamines with fatty acids, esters or triglycerides, which are useful for various consumer products and industrial applications

ABSTRACT

Amphoteric derivatives of aliphatic polyamines, such as diethylenetriamine or bis (hexamethylene) triamine reacted with long chain fatty acids, esters or triglycerides from various natural or synthetic sources are effective in the softening/texture modification of substrates such as paper, textiles, human skin surfaces and hair tresses, as well as in applications for metal working and lubrication. The polyamines are first reacted with fatty acids, esters or triglycerides derived from various animal, vegetable or synthetic sources ranging in molecular distribution from butyric through erucic acids (e.g. milkfat, soy bean oil, rapeseed oil) to form amidoamines or imidazolines; and are then further reacted with unsaturated or carboxylated epoxy compounds (e.g. acrylic acid, itaconic acid, verndic) to form the various amphoteric structures.

RELATED APPLICATION

This application is a continuation-in-part of application Ser. No. 09/136,936 filed Aug. 20, 1998, now U.S. Pat. No.6,004,914.

FIELD OF THE INVENTION

The present invention relates to amphoteric surface active agents, and more particularly to amphoteric derivatives of aliphatic triamines, such as diethylenetriamine and Bis (hexamethylene) triamine reacted with long chain fatty acids, esters or triglycerides. In addition to being novel materials, the amphoteric derivatives of this invention are useful in a variety of applications including the softening/texture modification of substrates such as paper, textiles, human skin surfaces and hair tresses, as well as in applications for metal working, and lubrication.

BACKGROUND OF THE INVENTION

Amphoteric compositions of various types including derivatives of polyamines are known and have been used over the years for a variety of applications including surfactants in detergent and dishwashing formulations, fabric and paper treating compositions, metal treating and corrosion inhibition, and the like. For example, U.S. Pat. No. 2,999,069 to Masci teaches detergent compositions containing amnphoteric derivatives of amidoamines but does not teach or disclose diamide or polyamide compositions having a reactive secondary, internal nitrogen amine site which is carboxyalkylated as provided in the present invention. Liquid dishwashing compositions disclosed in European Patent Application No. 92 203 230.5 to Jadwiga Palicka include amphoteric surface active agents; however, neither diamide nor polyamide compositions having a secondary, internal nitrogen amine site which is carboxyalkylated are disclosed by Palicka. U.S. Pat. No. 5,322,630 to Williams et al. discloses amphoteric derivatives of a broad range of fatty polyamines, fatty amidoamines, fatty imidazoline amines and polyamines which are employed as oilfield corrosion inhibitors. There is, however, no disclosure or suggestion in the Williams patent of the applications of the amphoteric derivatives of the polyamines herein disclosed, including neither the softening/texture modification of substrates such as paper, textiles, human skin surfaces and hair tresses, nor applications for metal working and lubrication.

Furthermore, providing non-irritating softening agents for fabric or paper substrates, or to human skin or hair, has been a long felt need. Fabrics tend to become slightly harsher after wear and laundering. Moreover, untreated personal hygiene facial tissue paper may be harsh and irritating to inflamed tissues, such as nasal orifice skin.

Various attempts have been made to soften fabrics such as suggested in patents directed to fabric softeners, for example, U.S. Pat. No. 3,904,533 of Neiditch for a liquid fabric softener, and U.S. Pat. No. 4,237,155 of Kardouche and U.S. Pat. No. 5,376,287 of Borcher et al which describe antistatic fabric softener sheets, which include fabric-softening agents, such as cationic and nonionic surfactants.

OBJECTS OF THE INVENTION

It is therefore an object of the present invention to define a family of amphoteric compounds comprising derivatives of aliphatic polyamines such as diethylenetriamine and Bis (hexamethylene) triamine wherein the polyamines are first converted to polyamides or imidazoline/amide derivatives thereof

A further object of the present invention is to define and describe a process by which the above described amphoteric derivatives of aliphatic polyamines [ADAPS] may be made.

It is another object of the present invention to provide an effective softener for various substrates such as paper and textile products which might contact human skin, as well as skin and hair substrates themselves.

It is a still further object of the present invention to provide amphoteric surface active agents for use in a variety of other applications, such as metal working, lubricating, etc.

SUMMARY OF THE INVENTION

The present invention relates to amphoteric derivatives of aliphatic polyamines [ADAPS] that have important industrial and personal care uses, such as, for example, softeners, lubricants, and conditioners, etc. The ADAPs comprise derivatives of compositions which are intermediate aliphatic polyamides or imidazolines, and preferably aliphatic diamides, derived from aliphatic diamines reacted with more than one substituent moiety selected from the group consisting of long alkyl chain fatty acids, esters and triglycerides, such as derived from animal, vegetable or synthetic sources ranging in molecular distribution from butyric through erucic acids. (e.g. milkfat, soybean oil, rapeseed oil).

The intermediate amide compound is then converted into an amphoteric compound by reacting it with unsaturated carboxylic acids or carboxylated epoxy compounds.

The carboxyalkylation step of the present invention attaches an alkyl carboxylic acid functional group to the secondary internal amine nitrogen atom, thereby forming the amphoteric products of the present invention. The amphoteric product is thus a polyamide or imidazoline derivative of the aliphatic polyamine starting material.

Compounds containing acidic functional groups suitable for use in reacting with aliphatic polyamides in accordance with the present invention include alkyl carboxyl groups i.e., carboxylic acid functional moiety, COOH where the carboxylic acid is derived from one or more unsaturated carboxylic acids or carboxylated epoxy compounds. For the purposes of the present invention such above-mentioned unsaturated carboxylic acids or carboxylated epoxy compounds comprise an amphoteric forming group because the product produced by reacting with one of the acids is an amphoteric product.

DETAILED DESCRIPTION OF THE INVENTION

Consistent with the above discussion, a first specific group of ADAPs of the present invention may comprise amphoteric derivatives of diethylenetriamine [DETA] wherein the amphoteric derivatives of the present invention are prepared by first reacting DETA as a starting material with at least one member selected from long-alkyl-chain plant, animal or synthetic derived fatty acids, esters and triglycerides, such as, for example, compositions containing substituted or unsubstituted, branched or straight chain, saturated or unsaturated alkyl chain groups ranging in molecular distribution from butyric through erucic acids, that is, containing from 3 to 21 carbon atoms in addition to the carboxyl group.

An intermediate substituted DETA predominately diamide is formed having fatty alkyl moieties of 3 to 21 carbon atoms.

The intermediate amide compound is then converted into an amphoteric compound by reacting it with unsaturated carboxylic acids or carboxylated epoxy compounds.

The carboxyalkylation step of the present invention attaches an alkyl carboxylic acid functional group to the secondary internal amine nitrogen atom, thereby forming the amphoteric products of the present invention. The amphoteric product is thus a polyamide or imidazoline derivative of the aliphatic polyamine starting material.

Amphoteric forming agents suitable for use in reacting with aliphatic polyamides in accordance with the present invention include alkyl carboxyl groups (i.e., carboxylic acid functional moiety, COOH) where the carboxylic acid is derived from one or more unsaturated carboxylic acids, or carboxylated epoxy compounds. Exemplary suitable amphoteric forming agents include vernolic acid, acrylic acid and itaconic acid.

The ADAPS of the present invention also comprise a group of compounds analogous to the above described DETA derivatives, that are amphoteric derivatives of Bis (hexamethylene) triamine. The foregoing discussion applies to such alternative triamines just as it does to DETA.

A third group of products having novel applications is comprised of amphoteric imidazolines which are prepared according to the method hereinafter described for preparation of the DETA derivatives.

The following general structural formulas numbers 1 through 2 comprise the novel compounds of the present invention, and are further exemplified and represented in Table 1 below.

Formula 1, below, generically shows diethylenetriamine [DETA] amphoteric derivatives more particularly set forth in Table 1 below. Formula 1 is a diamide, having an amide group at each end of the molecule. The central (secondary) nitrogen site on the molecule is further reacted to form the amphoteric end product of the present invention.

FORMULA 1

wherein:

R₁ is a saturated or unsaturated aliphatic mono or poly carboxylic acid moiety having one more carboxyl functional groups derived from intermediates containing olefinic or epoxy reactive sites, and may have one or more branched saturated or unsaturated, substituted or unsubstituted aliphatic chains containing from 2 to 18 carbon atoms;

R₂ and R₃, which may be the same or different, can be a straight or branched, saturated or unsaturated, substituted or unsubstituted alkyl chain of 3 to 21 carbon atoms; and

x is an integer of 1 to 5.

Formula 2, below is a generic DETA-derived imidazoline, where the acidic functional group making the molecule amphoteric is attached to the quaternary nitrogen. Formula 2 is more particularly set forth in Table 1 below.

wherein:

R₁ is a saturated or unsaturated aliphatic mono or poly carboxylic acid moiety having one or more carboxyl functional groups derived from intermediates containing olefinic or epoxy reactive sites, and may have one or more straight or branched, saturated or unsaturated, substituted or unsubstituted aliphatic chains containing from 2 to 18 carbon atoms; and

R₂ and R₃, which may be the same or different, can be a straight or branched, saturated or unsaturated, substituted or unsubstituted alkyl chain of 3 to 21 carbon atoms.

TABLE #1 Polyamine-Derived Amphoterics DETA Derivatives

I

II where

A or CH₂CH₂COOH B or

C where R₂ & R₃ = C₃H₇ to C₂₁H₄₃ G or C₃H₅ to C₂₁H₄₁ H

The diamide and imidazoline-amide intermediate compositions suitable for use in the preparation of amphoteric compositions of the present invention in accordance with the practice of the invention are well known and include those derived from substituted or unsubstituted, branched or straight chain, saturated or unsaturated fatty acids, esters, or triglycerides with fatty alkyl amide moieties containing from 4 to 22 carbon atoms. Examples of suitable fatty acids, esters or triglycerides include octanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, methyl esters or glyceride esters of such acids or mixtures thereof as are found in coconut oil, palm oil, sunflower oil, soybean oil, rapeseed oil, castor oil, fish oil, tallow fat, milk fat, lard and other natural sources or may be of synthetic origin.

The materials of the present invention are embodied in reactions carried out under the following conditions, as noted in the Examples below.

For example, amphoterics are derived from DETA-diamides, such as shown in Example 1 below, wherein linoleic-DETA diamide monopropionate is produced, from a two-step reaction wherein soybean oil and diethylenetriamine are first reacted, followed by a second reaction wherein acrylic acid is added.

In Example 2 below, oleic DETA diamide is produced by reaction of a mixture of olive oil and diethylenetriamine.

In Example 3 below, to the amide of example 2 there is added acrylic acid, to produce oleic DETA diamide monopropionate, or, as noted in Example 4 below, there is added itaconic acid, to produce oleic DETA diamide mono-3-carboxybutyrate.

As noted in Example 5 below, caprylic-capric-DETA diamide propionate is produced from the reaction of a mixture of caprylic-capric triglyceride and diethylenetriamine, which is further reacted with acrylic acid.

Furthermore, as noted in Example 6 below, dioleyl-imidazoline-amide-propionate is produced from two reactions, namely a reaction of a mixture of oleic acid and diethylenetriamine, which is further reacted with glacial acrylic acid.

The foregoing present invention includes aliphatic intermediate derivatives of polyamine compounds which result in amphoteric imidazolines or preferably diamides having a carboxyalkylated internal amine nitrogen site. Carboxyalkylation is achieved by reacting, as indicated hereinabove, a substituted triamine or diamide intermediate with an amphoteric-forming group consisting of unsaturated carboxylic acids or suitable carboxylated epoxy compounds.

The resulting compounds are useful as softeners for paper, tissues, fabrics, hair and skin, and a novel method of softening is disclosed based on the use of the compounds described herein. Because the novel compounds of the present invention provide antiwear properties, a method of using these compounds of the present invention in metal working is also taught.

It is therefore a further aspect of the invention to use the amphoteric derivative compositions of the invention, for example, as softening agents for paper such as facial tissue paper, textiles, hair and human skin in amounts of 0.1 to 10% by weight and for metal working applications such as lubricating and antiwear compositions in amounts of from about 0.1% by weight.

The invention is noted in the following illustrative examples, which are provided herein for the purposes of illustration only, and are not intended to limit the scope of the present invention, as noted in the appended claims.

Pertinent examples of preparation of the novel materials of the present invention are embodied in reactions carried out under the following conditions.

EXAMPLE 1 Linoleic-DETA Diamide Monopropionate

To a three-necked flask fitted with a stirrer, thermometer and reflux condenser is charged 584.0 gms. soybean oil and 103.0 gms. diethylenetriamine (DETA). The reaction mixture is heated at 180-190° C. for four hours, at which time the alkali value drops to 90 (mm KOH/g). After cooling to 70° C., 79.2 gms. acrylic acid was added. The addition is exothermic and the temperature rises to 102° C. The temperature is maintained at 90-100° C. for an additional four hours. After the reaction is complete, the final alkali value is 75, the acid value is 64 and the 10% pH in isopropyl alcohol/water is 4.8.

EXAMPLE 2 Oleic-DETA-Diamide

To a three-necked flask fitted with a stirrer, thermometer and reflux condenser is charged 584.0 gms olive oil and 103.0 gms diethylenetriamine [DETA]. The reaction mixture is heated at 180-190° C. for four hours at which time the alkali value drops to 90 (mm KOH/g).

EXAMPLE 3 Oleic-DETA Diamide-Monopropionate

To 68.7 gms of the amide of above Example 2 at 90° C., in a reaction vessel is charged 7.9 gms of acrylic acid. The mixture is heated with agitation at 95-105° C. for five hours until reaction is complete, as evidenced by disappearance of acrylic acid as measured by GC or HPLC determinations.

EXAMPLE 4 Oleic-DETA Diamide Mono-3-Carboxybutyrate

To 68.7 gms of the amide of Example 2 at 90° C. is charged 14.3 gms of solid itaconic acid. The mixture is heated with agitation at 95-105° C. for 5 hours, until reaction is complete, as evidenced by disappearance of itaconic acid as measured by GC or HPLC determinations.

EXAMPLE 5 Caprylic-Capric-DETA Diamide Propionate

To a three-necked flask fitted with a stirrer, thermometer and reflux condenser there is charged 330 gms of a caprylic capric-triglyceride, of the trade name Neobee M5, from Stepan Chemical Co., and 103 gms of diethylenetriamine. The mixture is heated at 180-185° C. for four hours, after which the alkali value dropped to 135 (mm KOH/g). After cooling to 70° C., 72 gms of acrylic acid are added and the mixture heated at 90-100° C. for four hours, until the reaction is complete, as evidenced by disappearance of acrylic acid as measured by GC or HPLC determinations.

EXAMPLE 6 Dioleyl-Imidazoline-Amide-Propionate

To a three-necked flask fitted with a stirrer, thermometer and distillation condenser there is charged 564 gms. of oleic acid and 103.2 gms of diethylenetriamine. The reaction mixture is heated to 155° C. where water of reaction begins to distill. The temperature is allowed to rise gradually to 190-200° C. over about three hours at which time the alkali value is 105.6 and the acid value is 4.10. Vacuum was then applied gradually until a pressure of 11 mm Hg is reached. Samples are taken periodically and checked for imidazoline content. After about three hours at 190° C. and 11 mm Hg, an imidazoline content of 90% is obtained. The product is then cooled to 70° C. and the vacuum is released. 72 gms of glacial acrylic acid is added. The exothermic reaction carried the temperature to 95° C., which is maintained for an additional 4 hours, until reaction is complete.

EXAMPLE 7 Milk Lipids-DETA Diamide Monopropionate

To a three-necked flask fitted with a stirrer, thermometer and reflux condenser is charged 490 gms. milk lipids and 103.0 gms. of diethylenetriamine (DETA). The reaction mixture is heated at 180-190° C. for four hours, at which time the alkali value drops to 93 (mm KOH/g). After cooling to 70°, 72 gms of acrylic acid is added. The addition is exothemic and the temperature rises to 102° C. The temperature is maintained at 90-100° C. for an additional four hours. After the reaction is complete, the final alkali value is 88, the acid value is 76 and the 10% pH in isopropyl alcohol/water is 65.

EXAMPLE 8 Milk Lipids-Imidazoline-Amide Dipropionate

To a three-necked flask fitted with a stirrer, thermometer and reflux condenser is charged 490 gms of milk lipids and 103 gms of diethylenetriamine (DETA). The reaction mixture is heated at 155° C. where water of reaction begins to distill. The temperature is allowed to rise gradually to 190-200° C. over about three hours, at which time the alkali value is 96 (mm KOH/g).

Vacuum is then applied gradually until a pressure of 11 mm of Hg is reached. Samples are taken periodically and checked for imidazoline content. After about three hours at 190° C. and 11 mm Hg, an imidazoline content of 90% is obtained. The product is cooled to 70° C. and the vacuum is released.

To the molten imidazoline is added 172 gms of methylacrylate (2 moles) and the mixture is heated at 90 to 100° C. for four hours. After which the methylacrylate content is less than 5%. The reaction mixture is charged to a separate flask containing a solution of 120 gms of 50% caustic soda, 522 gms of propylene glycol and 729 gms of water and heated at 90° to 95° C. for two hours to hydrolyze the methyl ester. After cooling to 50° C., the reaction product is a clear amber liquid with total solids of 34.6% having a 10% pH in isopropyl alcohol/water of 10.1.

EXAMPLE 9

Table #2 below outlines the procedure used, as well as the results obtained in evaluating several diethylenetriamine (DETA) amphoteric derivatives (Samples A-1, A-2, A-3 and A-4) for their softening properties on tissue paper.

The results of Table #2 indicate that all of the DETA-derived amphoterics tested (Samples A-1, A-2, A-3 and A-4) exhibited very good paper softening properties and are superior to the Control Sample 1, namely, a DETA imidazolinium quaternary derivative tested.

The amphoteric derivatives, Samples A-1, A-2, A-3 and A-4 in Table #2, are found to be very effective in softening challis wool swatches which are soaked in aqueous dispersions of the amphoterics and then rinsed and allowed to dry using the procedure similar to that used with facial tissue paper. It is also noted that the amphoteric derivative samples are effective in depositing a residual, smooth conditioned feeling to human skin and hair.

TABLE #2 Facial Tissue Softness Evaluations of Diethylenetriamine (DETA) Derivatives

Procedure:

1. 1% active test solutions/dispersions are prepared in deionized water and adjusted with lactic acid to the 4-8 pH range.

2. Evaluations are conducted using 8″×9″ untreated paper tissues weighing approximately 1.5 grams each. The lower half of each tissue is dipped briefly into the 1% active solution being tested, then the tissues are withdrawn, allowed to drain, dried and equilibrated for several hours at ambient temperature and humidity. A deionized water blank is included in the test regimen.

3. Treated tissues are evaluated (undipped versus dipped portions) and ranked for softness by a small R&D expert panel. Numerical softness rankings are assigned as follows:

0=Poor/harsh texture

1=Fair

2=Good

3=Very Good

4=Excellent/very soft texture

After Dipping in 1% Active Dispersions Followed by Draining and Drying

Softness/ 1% Active Material Tested In Water Texture Sample A-1 Milkfat DETA Imidazolinium 3.5 Amphomonopropionate Sample A-2 Soybean Oil DETA Diamide 3.5 Amphomonopropionate Sample A-3 Rapeseed Oil DETA Diamide 3 Amphomonopropionate Sample A-4 Milkfat DETA Imidazolinium 3/3.5 Amphodipropionate Control 1 Milkfat DETA Imidazolinium Quaternary 2.5 Control 2 Deionized Water Blank 0

All of the DETA amphoteric derivatives tested exhibit very good paper softening properties and are superior to the quaternary softener (Control 1).

EXAMPLE 10

Table #3 below shows a comparison of two DETA-derived amphoterics, Sample B-1, namely, a disoya DETA amphomonopropionate as prepared in Example 1 and Sample B-2, namely, a di-caprylic-capric DETA amphomonopropionate as prepared in Example 5 versus a Control, namely, a commercial milk lipid amido propyl betaine, when used in a bath and shower cleanser. The DETA derivatives of Samples B-1 and B-2 exhibit better conditioning on skin and hair, and better foam in the case of the caprylic-capric amphoteric than the Control, namely, milk lipid amido-propyl betaine.

TABLE #3 Bath and Shower Cleansers Soya & C8-10 DETA Diamide Amphoterics vs. Milk Lipid Amidopropyl Betaine R67.00-11A R67.00-11B R70.01-127 Raw Material % by Weight % by Weight % by Weight Deionized Water 45 45 45 Sodium Chloride 1 1 1 Sodium Lauryl Sulfate (28%) 10 10 10 MONALAC MPL 2 2 2 MONALAC MO 2 2 2 Sodium Laureth Sulfate (26%) 35 35 35 Milk Lipid Amidopropyl 5 — — Betaine (MONALAC MAB) Control Sample B-1 (Example 1) — 5 — Sample B-2 (Example 5) — — 5 The ingredients are added in the order listed. The pH is adjusted to 6.0-6.5. Clear yellow Opaque, Light Appearance: Clear Liquid Liquid Yellow Liquid Viscosity (ambient temp.): 2,000 cps 1,500 cps 1000 Viscosity with an 6,500 cps 3,500 cps 800 additional 0.25% NaCl: pH: 6.37 6.38 6.36

After washing, all of the products give a very smooth conditioned feel to the skin and hair, but the di-soya and di(C8-10) amphoterics, Sample B-1 and B-2, exhibit a higher level of smoothness than the milk lipid amidopropyl betaine. In addition, the di(C8-10) amphoteric (Sample B-2) exhibits much higher foam levels during washing.

Further application testing is carried out on polyamine amphoteric derivatives of the present invention in the areas of lubrication, hydraulic fluids, metalworking and anti-wear additives.

EXAMPLE 11

Table #4 below shows a list of Samples C-2 through C-8 tested for metal working, lubrication and anti-wear additives. The “structure type” refers to the chemical structure noted in Table 1 herein, wherein the Roman numerals refer to the basic molecular structure and the Alphabetical designations refer to the specific designations for the various “R” groups in the formulas of Table 1. Performance data are shown for experimental compositions evaluated in the zwitterionic acid forms, as well as the long chain alkylamine salts.

TABLE #4 DESCRIPTIONS OF SAMPLES TESTED For Metalworking & Hydraulic Fluid Additives Sample Structure Acid Form or Designation Type R₂ & R₃ Neutralizing Agent C-2 II C₁₇H₃₄ Tridecyloxypropylamine C-3 II C₁₇H₃₄ Acid Form C-4 I-C C₁₇H₃₄ Acid Form C-5 I-C C₁₇H₃₄ Tridecyloxypropylamine C-6 I-B C₁₇H₃₄ Tridecyloxypropylamine C-7 I-C C₁₇H₃₄ Tridecyloxypropylamine C-8 I-B Soya Acid Form

Table #5 below shows that in ASTM 2783, studies of blends with paraffinic and naphthenic derived mineral oils, marked decreases in steel ball scar diameters are noted for several of these derivatives.

TABLE #5 Results of Four-Ball Method Testing (ASTM Test Procedure D2783) 2% ZnDTP** Scar Added to Coef- Scar Sample Tested Dia- 0.1% ficient Dia- @ 0.1% in Coefficient meter in Mineral of Fric- meter Mineral Oil of Friction (mm.) Oil tion (mm.) C-6 0.0493 0.9 C-6 0.0586 0.5 C-7 0.0595 0.9 C-7 0.0510 0.4 C-2 0.0595 0.9 C-2 0.0782 0.5 C-5 0.0935 0.8 C-5 0.0773 0.5 Monacor 39* 0.0799 0.5 Monacor* 0.0595 0.5 39 ZnDTP 0.0952 0.6 alone *Commercial test products **Zinc dialkyl dithio phosphate 

What is claimed is:
 1. Texture and softening compositions for a wide range of paper, textile and human substrates comprising amphoteric compositions that are represented by the formula:

wherein: R₁ is a saturated or unsaturated aliphatic mono or dicarboxylic acid moiety having one or more carboxyl functional groups derived from intermediates containing olefinic or carboxylated epoxy reactive sites, and having one or more straight or branched, saturated or unsaturated aliphatic chains containing from 2 to 18 carbon atoms; R₂ and R₃, which may be the same or different, are straight or branched, saturated or unsaturated alkyl chains of 3 to 21 carbon atoms; and x is an integer of 2 to
 5. 2. Texture and softening compositions as in claim 1, wherein R₁ is derived from a carboxylic acid having an unsaturated alkyl carbon chain.
 3. Texture and softening compositions as in claim 1, wherein R₁ is a carboxylic acid functional group having an unsaturated alkyl carbon chain.
 4. Texture and softening compositions for a wide range of paper, textile and human substrates comprising amphoteric compositions represented by the general formula:

wherein: R₁ is a saturated or unsaturated aliphatic, mono or dicarboxylic acid moiety having one or more carboxyl functional groups derived from intermediates containing olefinic, or epoxy reactive sites, and having one or more straight or branched, saturated or unsaturated aliphatic chains containing from 2 to 18 carbon atoms; and R₂ and R₃, which may be the same or different, is a straight or branched, saturated or unsaturated alkyl chain of 3 to 21 carbon atoms.
 5. Texture and softening compositions as in claim 4, wherein, R₁ is an aliphatic mono or dicarboxylic acid moiety having one or more carboxyl functional groups, and wherein R₂ and R₃ are a straight or branched chain, saturated or unsaturated aliphatic chains having from 3 to 21 carbon atoms.
 6. Texture and softening compositions as in claim 4, wherein R₁ is derived from a carboxylic acid functional group having from 2 to 18 carbon atoms.
 7. Texture and softening compositions as in claim 4, wherein further, R₁ is a carboxylic acid functional group having an unsaturated alkyl carbon chain.
 8. A method of softening paper, textile and human substrates comprising contacting the substrate to be softened with compositions comprising an effective amount of the compositions of claim 1; and, permitting the object to dry.
 9. The method of claim 8 wherein the substrate to be softened is paper.
 10. The method of claim 8 wherein the substrate to be softened is textile fabric.
 11. A method of softening paper, textile and human substrates comprising contacting the substrate to be softened with compositions comprising an effective amount of the compositions of claim 4; and permitting the object to dry.
 12. Metal treating compositions comprising an effective amount of the composition of claim
 1. 13. Metal treating compositions comprising an effective amount of the composition of claim
 4. 14. Texture and softening compositions for a wide range of paper, textile and human substrates wherein an amphoteric surface active agent represented by the formula:

wherein: R₁ is a saturated aliphatic mono or dicarboxylic acid moiety having one or more carboxyl functional groups derived from intermediates containing olefinic or carboxylated epoxy reactive sites, and having one or more straight or branched saturated aliphatic chains containing from 2 to 8 carbon atoms; and R₂ and R₃, which may be the same or different are a straight or branched, saturated or unsaturated alkyl chains of 3 to 21 carbon atoms is present on paper, textile or human substrate.
 15. A method of softening paper, textile and human substrates comprising contacting the substrate to be softened with an effective amount of the amphoteric surface active agent of claim 14, and, permitting the object to dry.
 16. The method of claim 15 wherein the substrate to be softened is paper.
 17. The method of claim 15 wherein the substrate to be softened is textile fabric. 